Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 17-18, Pages 2549-2555Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700175
Keywords
asymmetric catalysis; Diels-Alder reaction; nitroolefins; organocatalysis; alpha,beta-unsaturated cyclic ketones
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The direct amine-catalyzed enantioselective Diels-Alder reaction between alpha,beta-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels-Alder reaction with high stereoselectivity and furnishes the corresponding Diels-Alder adducts in good to high yields with > 25:1 dr and up to 86 % ee. The study demonstrates a convenient entry to functionalized bi-cyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.
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